Benzo[<i>b</i>] thiophene derivatives. XVIII. The sulfur isosteres of harmaline, harmine and related isomers

Bosin, Talmage R.; Maickel, Roger P.; Dinner, A.; Snell, A.; Campaigne, E.

doi:10.1002/jhet.5570090614

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Cited by 6 publications

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Novel Benzo[b]thienylhydrazine and 1,3,4‐Oxadiazole Derivatives as Potential Antidepressant Agents

Aboulwafa

El-Metwalli

1992

Archiv der Pharmazie

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Three novel series of benzo[b]thiophene derivatives bearing various hydrazone, hydrazine and 1,3,4-oxadiazole moieties were synthesized as potential antidepressant agents. 22 Compounds were evaluated for their in vitro inhibitory effect on monoamine oxidase enzyme (MAO) type A. Several compounds inhibited MAO stronger than pargyline hydrochloride. Maximum inhibitions of 83% and 90% were observed with 1-benzyl-2-(3-chlorobenzo[b]thienyl-2-carbonyl)hydrazine (24) and 1-[2-(4-chlorophenyl)ethyl]-2-(3-chlorobenzo[b]thienyl-2- carbonyl)hydrazine (35), respectively.

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Novel Benzo[b]thienylhydrazine and 1,3,4‐Oxadiazole Derivatives as Potential Antidepressant Agents

Aboulwafa

El-Metwalli

1992

Archiv der Pharmazie

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ChemInform Abstract: BENZO(B)THIOPHEN‐DERIVATE 18. MITT. DIE SCHWEFEL‐ISOSTEREN VON HARMALIN, HARMIN UND AEHNLICHEN ISOMEREN

Bosin¹,

Maickel²,

Dinner³

et al. 1973

Chemischer Informationsdienst

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Benzo[b]thiophene derivatives. XXIII. Derivatives of 5,6‐dihydroxy‐3‐benzo[b] thienylacetic acid

Campaigne

Homfeld

Mais

1978

Journal of Heterocyclic Chem

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A series of 5,6‐disubstituted benzo[b]thiophenes have been synthesized for biological evaluation. These include analogs of tryptamine, melatonin and harmaline types, having hydroxy, methoxy, methoxymethyloxy, or isopropylidenedioxy groups at both the 5‐ and 6‐ positions. In order to synthesize these, the appropriate mercaptoguaiacols were prepared, and condensed with chloroacetoacetic esters to the 4‐arylthioacetoacetic esters. Cyclization of these ketones was best accomplished when the free phenolic groups were masked by methoxymethyl groups. The benzo[b] thienylacetic esters were then converted to corresponding amides, reduced to tryptamine analogs, acetylated to melatonin analogs, and cyclized to harmaline analogs. N‐Acetyltryptamine and 1‐methylmelatonin were also synthesized for comparison. Preliminary bioassay results on the melatonin analogs, which showed activity, are reported.

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Benzo[b] thiophene derivatives. XVIII. The sulfur isosteres of harmaline, harmine and related isomers

Cited by 6 publications

References 8 publications

Novel Benzo[b]thienylhydrazine and 1,3,4‐Oxadiazole Derivatives as Potential Antidepressant Agents

Novel Benzo[b]thienylhydrazine and 1,3,4‐Oxadiazole Derivatives as Potential Antidepressant Agents

ChemInform Abstract: BENZO(B)THIOPHEN‐DERIVATE 18. MITT. DIE SCHWEFEL‐ISOSTEREN VON HARMALIN, HARMIN UND AEHNLICHEN ISOMEREN

Benzo[b]thiophene derivatives. XXIII. Derivatives of 5,6‐dihydroxy‐3‐benzo[b] thienylacetic acid

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